Holiday rentals in Woodside

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Top-rated holiday rentals in Woodside

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Top guest favourite
A rustic treehouse is elevated on wooden stilts, surrounded by lush green trees. A spacious deck features several outdoor chairs for relaxation. Steps lead up to the entrance, while a cozy hammock is nestled beneath. The landscape includes a grassy area encouraging outdoor activities.
Treehouse in Bunker
4.96 out of 5 average rating, 160 reviews

Almost Heaven Treehouse

Featured in St Louis Magazine Spring 2022! Previously Parade Magazine and Only in Missouri! Nestled on the banks of Big Creek in the heart of the Missouri Ozarks and the Roger Pryor Pioneer Back Country, sits the Almost Heaven Treehouse. This quaint and rustic space is a must visit for those who love the great outdoors. Whether you want to relax in the creek, swim, hike, fish, paddle float,or ride atvs or s x s, this is the place for you!! This cabin is located 6 miles off pavement.

Top guest favourite
Home in Houston
4.99 out of 5 average rating, 269 reviews

Secluded Stone Cabin w/ Wood-Fired Hot Tub

Peaceful retreat to unplug and unwind. This off‑the‑grid experience has no electricity or flushing toilets, we do provide the essentials: running hot water, an outhouse, and propane lighting. Stay includes access to a handcrafted, wood‑fired hot. (Tub is still under construction. Landscaping and some final details are not finished.) Four-wheel-drive, or high-profile two-wheel drive vehicles are needed to get to the cabin. We must greet guests at arrival to show you how to use the propane lights.

Top guest favourite
The exterior view of the house highlights a covered deck with both seating and dining areas. A fire pit is visible in the yard, surrounded by a grassy space. The home features a light-colored facade under a metal roof, with trees dotting the background.
Home in Eminence
4.94 out of 5 average rating, 120 reviews

2 bedroom close to Jacks Fork and Current River

Rivertown Retreat is located less than 2miles from the Jacks Fork River and a short drive to the Current. This 2 bedroom home is the perfect place to get away from the busyness of life and relax. Sit on the porch swing, grill on the BBQ or toss the frisbee around in the large yard. Whether you are in Eminence for a float trip down the river, to hike in one of the many state parks close by, to catch some trout in the river or just to relax and enjoy the Ozarks, Rivertown Retreat is here for you!

Top guest favourite
Cabin in Cherokee Village
4.99 out of 5 average rating, 299 reviews

Hillside Haven secluded vintage cabin with hot tub

Enjoy the treehouse feel of this little 1966 cabin with summer shade and winter panoramic view of the bluffs. Couples will value the peaceful wooded location. Two Queen bedrooms and a Queen sofabed will accommodate up to 6. Grill and dine on the decks, soak in the hot tub on the private tin-roofed porch or roast marshmallows over the back yard fire pit. Close to South Fork and Spring rivers, golf courses, lakes, and historic Hardy town. Shop, float, fish, hike, golf, and explore the Ozarks!

Top guest favourite
A modern studio apartment is depicted from an outdoor angle, showcasing a vibrant green exterior. A wooden staircase with a railing leads to a second-level entrance. Gravel pathways surround the structure, and the sky is filled with clouds, suggesting evening light.
Place to stay in Cabool
4.98 out of 5 average rating, 167 reviews

COUNTRY LACE Retro Place

Our Country Lace Retro Place is a quaint little studio apartment nestled upstairs overlooking our rolling hills of the Ozark’s with abundant Wild Life (which can be scene early in the mornings or late evenings) and foliage ….furnished with a toaster, microwave, refrigerator, coffee maker and a Nija Flip up air fryer oven. Full bath with a furnished hair dryer and linens. Living space includes a king size bed, sofa and a oversized chair. We also have WIFI and our custom made retro TV….

Superhost
A small cabin exterior is shown, featuring a covered porch with green chairs and a small charcoal grill. The porch is framed by a wooden structure, with gravel pathways leading to a landscaped yard surrounded by trees.
Cabin in Eminence
4.78 out of 5 average rating, 181 reviews

Cabin Near the Ozark Rivers

Small cabin with its own private setting, just outside of city limits. 2.5 miles from town and the Jacks Fork River. Nice sized yard with a fireplace for your use. Plenty of on site parking and near by thousands of acres of public land. Whether you’re looking to float the river, recreate on public land, explore the caves and springs of Missouri, or just enjoy some peace and quiet, this is the place for you. The home is adjacent to Highway 106 on the west side of Eminence.

Top guest favourite
A charming cottage exterior is framed by a peaceful wooded setting. The screened porch features large windows, allowing for views of the natural surroundings. Potted plants enhance the entrance, alongside a rustic grill, while a welcome sign adds a personal touch to the inviting atmosphere.
Cottage in Summersville
4.99 out of 5 average rating, 118 reviews

Leona’s Cottage -Uniquely Rustic Comfortably Cozy

Leona’s Cottage is a unique hand built gem nestled in a peaceful wooded setting 2 miles down a quiet country road that’s surrounded by peaceful pastures and natural woodlands. The Cottage is a wonderful get-a-way for those looking for rustic charm but still wanting modern luxuries. Leona’s Cottage shares the road with Emily’s Cottage and is separated by a grove of trees far enough apart for total privacy but close enough for larger gatherings of up to 8 guests.

Top guest favourite
The barn conversion features a sloped roof with solar panels and a welcoming exterior. A gravel pathway leads to the entrance. A deck is visible on the upper level, surrounded by greenery, suggesting a peaceful country setting.
Barn in Houston
4.99 out of 5 average rating, 151 reviews

Old Dairy Barn

This former dairy barn sits on a farm that has been in our family for 150 years. It was our dream to turn it into a cozy, comfortable home that could be enjoyed by anyone needing a quiet country getaway. We are located close to Big Piney River, with river access from almost any direction, Piney River Brewing Company, Big Piney Sportsman's Club, Mark Twain National Forest and about 45 minutes to hour to several accesses on the Current and Jacks Fork Rivers.

Guest favourite
The exterior of the house features a welcoming front porch with wooden railings and steps leading to the entrance. Flanking the path, colorful flowers are arranged in pots. The surrounding area is adorned with trees, providing a natural backdrop.
Home in Mammoth Spring
4.84 out of 5 average rating, 190 reviews

The Archer House - 1 block from Spring River!

The Archer house is just two blocks from main street, one block from the Spring River, a short walk to Mammoth Spring State Park and close to dining and shopping. It has been completely remodeled in fall of 2022 and features many unique and premium features. Including a walk-in tile shower, wood ceilings in part of the house, cedar-clad front porch and more. The house is also equipped with brand new appliances, fast wifi, washer and dryer and more!.

Top guest favourite
A quaint cottage with a metal roof is surrounded by trees and open space. The structure is complemented by a nearby silo and a parking area with gravel. Natural light enhances the peaceful outdoor setting, with sparse landscaping and a picnic table visible in the foreground.
Cottage in Couch
4.98 out of 5 average rating, 126 reviews

Garfield Getaway LLC

Newly added 2nd bathroom and laundry attached to the cottage in a Grain Bin! Relax with the whole family in this peaceful country setting located approximately 10 miles from the beautiful Eleven Point River, well known for its canoeing, kayaking and fishing. Enjoy cooking on the grill and s’mores by the firepit. Also enjoy the Mark Twain National Forest with its beautiful hiking trails and natural springs. Party’s not allowed!

Guest favourite
A cabin is presented with a green exterior and a metal roof. A staircase leads to a balcony featuring two outdoor chairs. The surrounding area is lush with trees, providing a natural backdrop. A small outdoor seating area is visible at the base.
Cabin in Alton
4.91 out of 5 average rating, 180 reviews

Kayden’s Cabin

We are a family owned cabin near the Eleven Point River! We are located exactly 11 miles from the intersection of 19 North and 19 South in Alton, Missouri on AA Highway. Our cabin sleeps six people with a queen size bed, one set of bunk beds, full size blow-up mattress, and a loveseat. We are about a mile and a half from Whitten Access. Please No smoking, pets, or partying. **70.00 A Night**NO CLEANING FEE!!

Top guest favourite
A rustic cabin perched on stilts overlooks the Spring River, connected by a wooden staircase. An outdoor deck is adorned with red umbrellas, surrounded by lush greenery. A small area is visible at water level, enhancing the property’s direct river access.
Cabin in Hardy
4.95 out of 5 average rating, 124 reviews

Shipp’s Landing-Cozy Secluded Retreat on the water

Take it easy at this tranquil cabin getaway directly on the Spring River; ideal for trout/bass fishing, kayaking/tubing and relaxing. Indulge in the comfort of this off the beaten path retreat. Spacious back deck overlooking the water. Enjoy listening to the sounds of the river around the fire pit that comes stocked with complimentary wood, or show off your skills on the top deck with a charcoal grill!

Popular amenities for Woodside holiday rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Oregon County
  5. Woodside